Ossining Holidays from AU$3,137
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Your Ossining Holiday
With one of our holiday packages to Ossining, you'll find countless opportunities for fun and relaxation. There's tons to experience, including its rich history and spectacular views. Make your trip to Ossining even more fun by going sightseeing. Van Cortlandt Manor, Sleepy Hollow Cemetery and Tarrytown Music Hall are among the popular attractions worth exploring. Don't delay your visit to this city any longer. Your ultimate Ossining holiday is only a few clicks away with Expedia.
The Latest Ossining Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Beacon
Manhattan
AU$3,137
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.4/10 Exceptional! (1,530 reviews)
Enjoyed our stay here. It’s an older building but they maintain it nicely. Staff was very friendly and helpful. Great location for UWS
Reviewed on 11 Oct 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
AU$4,951
per person
26 Nov - 3 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.2/10 Wonderful! (4,026 reviews)
Walking to all the tourist sites. Area was safe. Staff was very helpful especially in arranging our transportation to the airport. Room was very clean.
Reviewed on 12 Oct 2026
Ossining Holiday
Ossining Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Population | 25,400 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre |
Our pick of the best Ossining Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
AU$241
8 Nov - 9 Nov
includes taxes & fees
8.6/10 Excellent! (257 reviews)
"Very quiet clean and peaceful. Do know the only downfall is very little food options including no vending machines. Plenty of options outside of the actual resort but be warned if you don't want to drive out."
Reviewed on 11 Oct 2026
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
AU$212
14 Oct - 15 Oct
includes taxes & fees
7.2/10 Good! (1,143 reviews)
"I was there late after 1 am to check in. No parking spot available even on the street. The area was unsafe. The environment is bad. No one at reception counter. Called three times with no response. This is really bad experience at middle of the night. We had to go to the other hotel in a hard time. ..."
Reviewed on 11 Oct 2026
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
AU$221
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very good! (1,885 reviews)
"For the price of the room this hotel was a disappointment. Our door didn't completely close and had gaps large enough to see light through, the bathroom light was coming out of the ceiling, the pool was freezing, the microwave in room was filthy and the breakfast was disgusting!"
Reviewed on 11 Oct 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Ossining attractions
Travelers Rest
This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
Photo by louann ohora
Teatown Lake Reservation
This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.
Ossining Historical Society
This intimate museum preserves Ossining's heritage through artefacts connected to Sing Sing Prison and local history. Schedule a personalised appointment for the most enriching exploration of this community treasure.
Sing Sing Prison Museum
Step inside America's most infamous prison at the Sing Sing Prison Museum, opening in 2025 for its 200th anniversary. Explore artefacts and stories illuminating incarceration and rehabilitation in America.
Kitchawan Preserve
Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Louis Engel Waterfront Park
Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Hudson Hills Golf Course
Nestled in Ossining's rolling terrain, this Mark Mungeam-designed course challenges players with strategic bunkers and undulating fairways. Enjoy Hudson River Valley views while navigating the thoughtful 18 holes.
Ossining Public Library
Learn about the local history of Ossining when you take a trip to Ossining Public Library. Amble around the area's parks or visit its monuments.
Frequently asked questions
How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from AU$3,137 on Expedia. However, how much your holiday to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you're hoping to keep costs down. Another tip for scoring cheap Ossining holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining holiday, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighbourhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining holiday itinerary.
Is it worth booking a holiday package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining holiday off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Use Expedia's handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book an Ossining holiday as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossining?
- Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
- Budget wisely: Besides the price of your accommodation, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
- Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Ossining. Then, estimate how long you'll need at each, including any travel time.
- Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Ossining holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
